LEWIS ACID-CATALYZED REARRANGEMENT REDUCTION OF 1-PHENYLOXIRANEMETHANAMINES - SYNTHESIS OF BETA-PHENETHYLAMINES/

Authors
HARDEN RC HODGKINSON TJ MCKILLOP A PROWSE WG URQUHART MWJ
Citation
Rc. Harden et al., LEWIS ACID-CATALYZED REARRANGEMENT REDUCTION OF 1-PHENYLOXIRANEMETHANAMINES - SYNTHESIS OF BETA-PHENETHYLAMINES/, Tetrahedron, 53(1), 1997, pp. 21-36
Citations number
22
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
53
Issue
1
Year of publication
1997
Pages
21 - 36
Database
ISI
SICI code
0040-4020(1997)53:1<21:LARRO1>2.0.ZU;2-B
Abstract
A range of 1-phenyloxiranemethanamines has been prepared and their rea ctions with sodium cyanoborohydride under boron trifluoride catalysis have been investigated. In general the products were the corresponding 2-amino-3-phenylpropan-1-ols derived from Lewis acid-mediated ring op ening of the epoxide in an aza-Payne manner and benzylic reduction of the intermediate aziridinium species. Copyright (C) 1996 Elsevier Scie nce Ltd